Because of these two truths, when shoes are bad, they're really horrendous. Alternatively, when they're great, they're wonderful. Impressive, even.

And that's what we're going for here. Impressive.

Business Insider reached out to its friends in the world of men's fashion — Judah Estreicher of custom suit shop JBD Clothiers, and designer Jesse Chao at Vittorio J — to put together a quick guide to buying a pair of men's dress shoes this season. In it, you'll find a few pointers about what's trending, some gorgeous examples of them, and then those same styles at a more ... conservative price point.

But first, lets talk basics. If you're buying a good quality shoe, all the materials should be organic, nothing synthetic. The soles should be stitched onto the shoe, never glued. You want that stitching through the sole into the shoe, and around the entirety of the shoe.

If you're buy good quality shoes, they'll last a long time if they're taken care of. Buy a polishing kit, take your shoes to get resoled, and be good to them. That should go without saying.

Now for what's trending.

"For this season it's about the military inspired dress boot," said Etreicher. "Double monk strap and wingtip are all styles which you can get away with dress or casual. In addition, people are wearing a combination of military inspired dress boot with wingtips."

This season, you'll also see a lot of suede, a pop of color, and some two-toned shoes.

Now, if you have upwards of $550 to spend on a pair of shoes, Chao recommends that you check out New York based shoe store Leffot. The shoes are impeccable (we used some for this story, and yes... they are sick). Estreicher showed us some smoke-shows from Scarpe di Bianco (same price point. Be careful out there).

For the rest of you there's anything from awesome boutique Jack Erwin — where shoes and boots are all under $215 — to Johston and Murphy, Allen Edmonds, and even Aldo as long as you know what you're looking for — and that's quality.

Now for the dos and don'ts — we have to have those or else it's no fun.

"My biggest advice would be if you're going to spend money on a nice pair of shoes, make sure it is color brown," says Chao. "Brown shoes match almost every color suit (except for black) and look great with jeans. The only times I have ever worn black shoes, have been with a tuxedo."

Page 2 of 2 - For Estreicher, there's nothing worse than "unkempt shoes with gaudy buckles while wearing a suit, or casual shoes with dress clothing."

Don't do that stuff. A few suggestions on how to do it below.Even the least adventurous of you can go with a basic black wing tip. These are gorgeous and cost $775.